51570-52-6

Basic information

• Product Name: 2-benzyl-N-methylaniline
• Synonyms: 2-benzyl-N-methylaniline
• CAS NO: 51570-52-6
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.2756
• Mol File: 51570-52-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 329.8°Cat760mmHg
• Flash Point: 161°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 0.000173mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 2-benzyl-N-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl-N-methylaniline(51570-52-6)
• EPA Substance Registry System: 2-benzyl-N-methylaniline(51570-52-6)

Safety Data

• Hazardous Substances Data: 51570-52-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 18, p. 1035, 1988 DOI: 10.1080/00397918808060888

InChI:InChI=1/C14H15N/c1-15-14-10-6-5-9-13(14)11-12-7-3-2-4-8-12/h2-10,15H,11H2,1H3

Upstream product

• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 2116-62-3 2-(2-phenylethyl)pyridine 
• 6590-44-9 N-methyl-N-(2-methylphenyl)aniline 
• 28059-64-5 2-benzylaniline 
• 67-68-5 dimethyl sulfoxide 
• 119515-87-6 o-bromo-N-methyl-N-allyloxyaniline 
• 119515-88-7 N-(2-bromophenyl)-N-methyl-O-propylhydroxylamine 
• 71492-76-7 N-allyl-N-methyl-2-bromoaniline 
• 100-39-0 benzyl bromide 
• 119515-90-1 N-(2-Benzyl-phenyl)-N-methyl-O-propyl-hydroxylamine 
• 81734-60-3 1-methyl-2-(2-phenylethyl)pyridinium iodide 

Downstream Products

• 260-94-6 acridine 
• 948-65-2 2-phenyl-indole 
• 120-12-7 anthracene 
• 102166-80-3 2-benzyl-N-methyl-N-(1-methyl-pyrrolidin-3-ylmethyl)-aniline 
• 113951-41-0 N-(2-benzyl-phenyl)-N,N',N'-trimethyl-propanediyldiamine 
• 101737-52-4 N-(2-benzyl-phenyl)-N,N',N'-trimethyl-ethylenediamine 

Relevant articles and documents

Radical and ionic mechanisms in rearrangements of o-tolyl aryl ethers and amines initiated by the Grubbs-stoltz reagent, et3SiH/KOtbu

Rearrangements of o-tolyl aryl ethers, amines, and sulfides with the Grubbs-Stoltz reagent (Et3SiH + KOtBu) were recently announced, in which the ethers were converted to o-hydroxydiarylmethanes, while the (o-tol)(Ar)NH amines were transformed into dihydroacridines. Radical mechanisms were proposed, based on prior evidence for triethylsilyl radicals in this reagent system. A detailed computational investigation of the rearrangements of the aryl tolyl ethers now instead supports an anionic Truce-Smiles rearrangement, where the initial benzyl anion can be formed by either of two pathways: (i) direct deprotonation of the tolyl methyl group under basic conditions or (ii) electron transfer to an initially formed benzyl radical. By contrast, the rearrangements of o-tolyl aryl amines depend on the nature of the amine. Secondary amines undergo deprotonation of the N-H followed by a radical rearrangement, to form dihydroacridines, while tertiary amines form both dihydroacridines and diarylmethanes through radical and/or anionic pathways. Overall, this study highlights the competition between the reactive intermediates formed by the Et3SiH/KOtBu system.

A SYNTHETIC EQUIVALENT FOR ORTHO-LITHIO-N-METHYLANILINE

o-Bromo-N-methyl-N-n-propoxyaniline undergoes halogen-metal exchange with butyllithium and the resulting lithio species reacts cleanly with a variety of electrophiles.The N-O bond of these products can be reduced with Raney nickel to afford ortho-substituted-N-methylanilines.

Recyclization of 2-(2-Phenylethyl)pyridinium Salts

Under the influence of aqueous solutions of alkylammonium sulfites 2-(2-phenylethyl)pyridinium salts undergo recyclization to 2-benzyl-N-alkylanilines.The effect of structural factors on the transamination, which takes place when a reagent with an alkyl g